Information Technology Jobs in Chicago Flexible

Our client is a forward-thinking consultancy at the forefront of technology and innovation, dedicated to empowering organizations to thrive in an ever-evolving digital landscape. Our clients mission is to help businesses harness the power of data and artificial intelligence to drive growth, enhance customer experiences, and optimize operations.

As they enter their next phase of expansion, they are seeking a GenAI Architect to drive cutting-edge AI/ML projects and turn complex data into actionable insights. You’ll thrive in a client-facing, project-based role, leading teams to design, build, and deploy enterprise-scale models across diverse use cases.

Responsibilities

• Lead project teams and act as the technical architect on AI/ML initiatives.
• Analyze large, complex datasets and translate them into impactful insights using ML and AI techniques.
• Build, implement, and deploy models into production environments, leveraging best practices across cloud and on-prem solutions.
• Collaborate with clients to define requirements, architect solutions, and present technical recommendations.
• Coach and mentor junior team members while driving project success.

Experience

• Proven track record building large-scale AI/ML solutions in enterprise or consulting environments.
• 5+ years of hands-on experience in statistical modelling, analytics, and machine learning.
• Advanced academic background (Master’s in Statistics, Math, Computer Science, or related; PhD is a strong plus).
• Expertise in a wide range of ML and AI techniques: regression models, cluster analysis, predictive modeling, neural networks, deep learning, decision trees, ensemble methods, and more.
• Strong programming skills in Python, TensorFlow, PyTorch, Hugging Face Transformers, and other ML frameworks for model development and experimentation.
• Deep understanding of NLP fundamentals, including tokenization, embeddings, language modeling, sequence labeling, and text generation.
• Experience with modern AI tooling: LangChain, vector databases, prompt engineering, and large-scale data embedding.
• Solid knowledge of relational (SQL) and non-relational (NoSQL) databases, and distributed systems like Hadoop and Spark.
• Ability to turn complex datasets into compelling, actionable insights using visualization tools (RShiny, Python, Tableau, Power BI, D3.js, etc.).
• Passion for mentoring and leading teams, fostering growth and knowledge sharing.
• Experience managing data workflows: wrangling, exploring, transforming, and analyzing diverse datasets.
• Familiarity with monitoring model performance, tuning, and ensuring high-quality data.
• Excellent communication skills with the ability to engage stakeholders at both technical and business levels.
• Strong curiosity and thought leadership, staying ahead of AI/ML trends and research.
• Experience deploying ML models into production on cloud platforms such as Google Cloud Platform, Azure, or AWS.

Please note, our client is unable to support visa transfers at this stage and can hire US citizens or Greencard holders.

If you feel you have the required skills, please get in touch with a copy of your CV! Or email me directly at

At Quotacom, we take the security and privacy of your personal data very seriously, any data we hold will be in accordance with data protection legislation. Full details of our privacy notice can be found at

AI Strategist

Senior Director, Consulting & Delivery

Level & Department

The honest version of what's happening in enterprise AI in the middle market ($100M - $2B) right now is messy. Most organizations know they need to move. Very few have the leadership that can operate fluently at both ends of the problem… the C-suite conversation about investment rationale and the engineering conversation about whether the architecture can actually support what was just promised.

That gap is expensive and we've seen it in every sector we work in. It shows up the same way every time: smart strategy work that doesn't connect to anything deployable, or capable technical teams building things that never get funded or adopted.

The Principal AI Strategist role exists to close that gap on our most important engagements.

THE ROLE

What this position actually does

You are the senior-most strategy and delivery mind on a client engagement. You hold the intellectual and commercial thread across the entire lifecycle from the first diagnostic conversation through to a working AI system in production and the expansion that follows when the client realizes it's changing something real.

You are not the person who manages the team to do the thinking… you are responsible for the most strategic form of that thinking. You shape the strategy, challenge the architecture, own the executive relationship, and are personally accountable for whether the engagement creates measurable business value.

The title is Principal AI Strategist because that's the actual job. The level is Senior Director because that reflects the scope, accountability, and authority this role carries inside Quantum Rise and in front of clients.

OUR OPERATING PRINCIPLES

The intellectual framework you'll work inside

Quantum Rise operates from a set of principles we call Consulting 2.0. They define how engagements are structured, how we challenge client assumptions, and what we hold ourselves accountable to.

Think like an investor, not a technologist

AI value is relative to each client’s own goals / circumstances and capital is precious. We anchor every engagement to strategy → value streams → enterprise value. We don't start with use cases. We start with where the business makes and loses money, and work backward to where AI creates leverage.

• Map to where the work actually happens: We go to L4–L5 process depth where the task-level execution that explains KPI performance and reveals where AI readiness actually exists.
• Diagnose before prescribing: We use structured diagnostic lenses (process, data, systems) to move from visible symptoms to root causes.
• Data reality bounds AI ambition: What AI can reliably do is determined by the strength of the data foundation (architecture, integration, quality, consumption) not by model choice.
• Not all AI systems are created equal: Machine learning, LLMs, and agents introduce different capabilities, constraints, and operational trade-offs. Enterprise-ready agents specifically require probabilistic reasoning balanced with deterministic rules, structure, guardrails, and human oversight.
• Risk is predictable: Enterprise AI risk falls into defined categories: data privacy, bias, explainability, and governance. Principles define what good looks like; governance establishes ownership, decision rights, and escalation.
• Execution credibility matters as much as technical ambition: “Crawl”and MVP solutions that are in production beat “Run” enterprise-wide solutions that aren't.

RESPONSIBILITIES

What you own

Client strategy and delivery

• Lead end-to-end engagement execution from strategy and diagnostic through deployment and commercial expansion
• Run executive discovery sessions translating ambiguous business problems into structured AI investment rationales
• Build the business case with the rigor of an investor, not the optimism of a vendor: quantified value, honest constraints, sequenced roadmap
• Own the relationship with C-suite and senior client stakeholders as a peer, not a service provider

Technical leadership

• Apply working fluency in LLMs, agentic workflows, RAG architecture, and data infrastructure to make real design decisions ensuring the original business value is obtained
• Collaborate with engineering to challenge, refine, and pressure-test solutions against production realities
• Define AI product roadmaps that are incrementally value generating, governed, measured, and adopted

Firm development

• Identify capability and offering gaps where Quantum Rise can build durable competitive advantage
• Build reusable delivery IP (frameworks, playbooks, diagnostic tools) that improve every engagement that follows
• Develop and mentor the next generation of AI consultants on what it means to operate at the intersection of AI strategy and delivery
• Contribute to business development through the quality of your work and the depth of your client relationships

THE PROFILE

Who fits here

person who thrives in this role has a particular combination that's genuinely rare and we'd rather name it honestly than let both sides waste time discovering the mismatch.

Dimension: What this looks like in practice

Role identity: You think of yourself as a strategist who builds things, not a consultant who advises on them.

Technical depth: Hands-on with LLMs and agentic coding. You've debugged a pipeline at some point and don't need to be reminded why hallucination is an enterprise risk.

Business fluency: You can translate AI capability into a CFO-ready investment case without losing the technical precision that makes it credible.

Delivery record: 12+ years in management consulting or technical advisory with real end-to-end accountability from scoping through go-live. You are hyper customer service oriented.

Sector context: You have meaningfully operated across 3 discrete sectors learning to how effectively understand how money is actually made, customer and demand dynamics, how work gets done, regulatory constraints, etc.

Education: Engineering, CS, or MIS undergraduate foundation. MBA preferred. The combination matters and what makes the translation instinct natural. What matters is the ability to translate value creation into technology and vice versa.

Working style: You reach for the AI tool first because it's genuinely how you think and not just because we’re an AI consultancy.

BENEFITS

What we offer

• Competitive base salary + variable compensation tied to individual and company performance
• Equity options
• BCBS health, vision, and dental
• 401(k) with discretionary annual match
• FSA, DCA, commuter, and L&D stipends
• Unlimited PTO + paid holidays + paid sick time

Rheinmetall 4iG Digital Services (R4) is a joint venture between Rheinmetall, a globally leading supplier of defense and automotive products, and 4iG, Hungary's leading IT systems integrator. R4 has been founded end of 2022 with its headquarters in Budapest and the initial mission to provide project- and operations-related IT services to Rheinmetall's local subsidiaries in Hungary and worldwide. Based on business requirements and opportunities, R4 plans to progressively expand the scope of its services for internal and external customers alike. In a nutshell, R4 is like a start-up with guaranteed success. Equipped with a hands-on mentality, it significantly benefits from the support and tremendous growth of both Rheinmetall and 4iG. The designated business and solid setup offer outstanding development potentials for R4 itself but consequently also for all employees, because there will be lots of interesting jobs in an international and dynamic work environment.

In order to achieve our common goals, we count on you

* Design, implementation and operation of print management system and print servers.

* Takes over communication with the service provider and processes reported problems in close cooperation with the service provider

* Approves the system settings for the printing functions provided by the service provider and ensures that they are maintained

* Improves existing processes and technical solutions

* Is an active member of the team and contributes to continuous optimization with their experience

What you will need for successful work

* Degree in computer science, information technology, business information technology, or related field with relevant working experience

* Professional experience (min. 3 years) with print servers and printing solutions (follow me printing)

* Professional experience with printer hardware (especially Konica Minolta printers)

* Thorough knowledge of modern print management software

* Basic knowledge of networks, databases and application servers

* Recognising and communicating technical, structural and organisational problems and developing proactive solutions

* Close cooperation with other departments within the organisation

* Thorough work ethic with attention to detail

* Strong analytical skills combined with a strong service and customer focus

* Independent, proactive work

* Positive and solution-oriented mindset, team spirit

* Business fluent English and Hungarian, both written and spoken

What we offer

* Take over an important and challenging role with high visibility

* Become part of the unique growth stories of Rheinmetall and 4iG, which offer outstanding development and career opportunities

* Gain insight into the defense and automotive industry

* Make use of the broad network with over 30.000 great colleagues at Rheinmetall and 4iG worldwide

* Benefit from various professional trainings and events

* Enjoy our international and flexible work environment with an official office in Budapest but up to 100% mobile work

What we are happy about

* Experience with SafeQ, Siteaudit, and Autostore systems

* Knowledge of ITIL processes

* Experience with ServiceNow

* Software release management

* German language skills are an advantage

Technical Sales Representative | Entry-Level | Full-Time

Training Classes Begin in July 2026

Ready to start your career in tech sales—without waiting years for real responsibility?

Join a global leader in automation and technology, known for its innovation, career growth, and hands-on sales training. If you’re a recent college graduate (or have 0–2 years of experience), this is your launchpad.

Why You’ll Love This Role:

• You’ll be in the field—meeting customers, solving problems, and making an impact from day one.
• You’ll receive paid, structured training designed for new grads, with mentorship throughout your first year.
• You’ll build a career, not just a job—with real income, fast promotion potential, and a global brand on your résumé.

What You’ll Do:

• Learn how to sell complex, technical products that power the modern factory
• Meet face-to-face with customers to understand their challenges and present solutions
• Cold call, follow up on inbound leads, and develop relationships with decision-makers
• Partner with your local office team to grow your regional territory

What You’ll Get:

• Base Salary: $54,000 – $81,000 (based on location)
• Quarterly Bonus Potential: Up to $24,000 annually
• Benefits: Medical, dental, vision, 401(k) with match, and ~4 weeks PTO
• Paid Training & Mentorship: Extensive onboarding + territory coaching
• Clear Promotion Path: Regular base and bonus increases tied to performance

Who We’re Looking For:

• Recent college grads or early career professionals (0–2 years experience)
• Bachelor’s degree required (or Associate’s + 4+ years of military service)
• Curious, driven, and willing to learn technical product knowledge
• Able to travel 60%+, including overnight trips
• Valid driver’s license and reliable vehicle
• Comfortable lifting and carrying demo equipment (35–85 lbs.)

Why Join This Company?

• Forbes “Most Innovative Companies” honoree
• 25+ years of 40%+ operating profit
• Promote-from-within culture built for high performers
• Global reach, startup energy, and real responsibility—fast

Apply now to secure your spot in the January or July 2026 training class.

We’re hiring now and reviewing applications on a rolling basis.

Com-.pet-i-tive: as good as or better than others of a comparable nature.

Company: Connect Search LLC

Title: Recruiter

About the job:

Connect Search has immediate openings for Recruiters for our Chicagoland office. We continue to experience tremendous growth, despite the current climate, and would like to add a Recruiter to our team immediately. To be successful, this person must be hard-working, motivated, and determined to build out their network to establish their business.

The ideal candidate will be comfortable meeting new people frequently and have an ability to determine a candidate's potential through relationship building and alignment of their goals. They should have excellent organizational skills to build and maintain a pipeline of prospective candidates. Additionally, they should be committed to both meeting and exceeding assigned quotas.

Responsibilities:

· Be accountable for enhancing the recruitment team's ability to rapidly target, identify, source, and present top talent for current and future searches

· Maintain and develop active candidates through name generation, networking, cold calling, complex internet searches and research

· Conduct virtual interviews or face-to-face meetings to learn more about the individual’s compensation requirements, personality, location requirements, and other aspects that will help us find them a better and/or new job

· Qualify or reject candidates based on interview feedback and resume reviews

· Effectively manage candidate and client process including assessments, interview coordination, and offer negotiation

· Meet weekly quotas related to calls and emails

Qualifications:

· Bachelor's Degree Preferred

· High-energy and passion

· Effective written and verbal communication skills

· Outstanding organizational skills, can work independently, and a close attention to detail

· Detail oriented, highly organized, able to multitask

· Demonstrated ability to thrive in a fast-paced environment

· Experience working with Microsoft Office Suite

About Connect Search:

Connect Search is a Chicago-based, award-winning staffing firm made of tenured recruiters who came together with a shared vision of providing the highest level of service to clients and candidates. Our founding partners offer profound networks in Information Technology, Finance & Accounting, Administrative, and Executive Search. Our services include contract, contract-to-hire, and permanent placement across all divisions.

Why Connect Search?

Connect Search offers full medical, dental, and vision insurance, and matches your 401K contributions. We also provide our employees a generous vacation package and now offer unlimited PTO starting on your first day! You will also be eligible for multiple bonuses and other perks as you progress with our organization.

Seeking a role that will allow you to work from home while making a difference in the world of technology? Are you someone who is passionate about technology and enjoys staying ahead of the tech curve? Are you looking for a role that offers flexible hours that will fit around your current schedule? Then we have a role for you!

TELUS Digital are currently hiring for a Personalized Ads Evaluator role! This is a freelance, independent contractor position that offers up to 20 hours per week.

In this role, you will be reviewing online advertisements by rating them on their relevance to the search terms used as well as providing feedback on their language and cultural relevance in order to improve their content, quality, and layout

Your ultimate goal will be to contribute towards making internet search and online advertising more relevant and interesting for millions of users, including yourself.

Join our team today and start putting your skills to work for one of the world's leading online advertising platforms while being a part of a supportive community that offers:

• Access to complimentary mental health support benefits like free EAP and Mindfulness Apps.
• Dedicated, responsive well-being team proactively offering well-being education each month, as well as quarterly initiatives.

Qualification path

No previous professional experience is required to apply to this role, however, working on this project will require you to pass the basic requirements and go through a standard assessment process. This is a part-time long-term project and your work will be subject to our standard quality assurance checks during the term of this agreement.

Basic Requirements

• Excellent communication skills with full professional proficiency in English
• Being a resident in USA for the last 3 consecutive years and having familiarity with current and historical business, media, sport, news, social media, and cultural affairs in Country
• Active use of Gmail, Google+, and other forms of social media and experience in the use of web browsers to navigate and interact with a variety of content
• Daily access to a broadband internet connection, a smartphone (Android 4.1, iOS 8 or higher), and a personal computer with antivirus software to work on. You’ll also need a Barcode Scanner application to be installed on your smartphone to complete certain tasks.

Assessment

In order to be hired into the program, you’ll be required to take an open book qualification exam that will determine your suitability for the position. You will also be required to complete and pass an ID verification process. Don’t worry, our team will provide you with guidelines and learning materials before your exam. You will be required to complete the exam in a specific timeframe but at your own convenience!

Join Our Team as a Website Tester at Little Wheel

Little Wheel is a gambling technology company focused on researching and building products that put players first. We are currently hiring Website Testers across Michigan, New Jersey, Pennsylvania, and West Virginia.

This is a great opportunity to earn extra income on a flexible schedule while helping us test online casinos. No prior experience is required, and all training is provided.

This is a short-term contract, with opportunities for ongoing work for high performers.

Role Overview

As a Website Tester, you will:

• Participate in user experience testing on various online casino platforms.
• Follow step-by-step instructions to complete assigned tasks.
• Record feedback and report bugs or usability issues.
• Provide detailed insights into your testing experience.
• Complete all testing assignments within set timelines.

Requirements

To be eligible, you must:

• Be at least 21 years old.
• Reside in one of the following states: Michigan, New Jersey, Pennsylvania, or West Virginia.
• Own a laptop or desktop computer.
• Be able to complete a short, paid online training and onboarding process.

No previous testing or gambling experience is needed. You will not be gambling with your own money, and there are no fees or out-of-pocket costs. All the interactions/game-play would be for testing purposes.

Compensation and Benefits

• Guaranteed earnings of at least $1,000 for approximately 20 hours of testing.
• Minimum of $25/hour, with higher pay for faster testers.
• $100 bonus upon completing the onboarding program.
• Flexible schedule – choose when you want to work.
• Work from home – test websites from the comfort of your own space.
• Fast payments – get paid after each of the 4 testing stages.
• Excellent support – coordinators available daily from 6 AM to 11 PM ET.

What Our Testers Say

"Great side gig for some extra cash. The team is very communicative and will answer any questions/concerns!" – Maria, Trustpilot (2021)

"Tasks are clearly explained with step-by-step instructions. You can work when it's convenient. Support is very helpful and responsive." – Anonymous, Glassdoor (2025)

Read more reviews on Glassdoor, Trustpilot, and Google.

Equal Opportunity Statement

Little Wheel LLC is proud to be an Equal Opportunity Employer. We are committed to creating an inclusive environment for all applicants and employees, regardless of race, religion, color, national origin, gender identity, sexual orientation, age, disability, or veteran status. We celebrate diversity and strive to create a workplace where everyone feels valued.

Company Info

Website: Address: Little Wheel LLC, 250 Pehle Ave, Suite 200, Saddle Brook, NJ 07663 Phone: (833) 313-7490

Join Our Team as a Website Tester at Little Wheel

Little Wheel is a gambling technology company focused on researching and building products that put players first. We are currently hiring Website Testers across Michigan, New Jersey, Pennsylvania, and West Virginia.

This is a great opportunity to earn extra income on a flexible schedule while helping us test online casinos. No prior experience is required, and all training is provided.

This is a short-term contract, with opportunities for ongoing work for high performers.

Role Overview

As a Website Tester, you will:

• Participate in user experience testing on various online casino platforms.
• Follow step-by-step instructions to complete assigned tasks.
• Record feedback and report bugs or usability issues.
• Provide detailed insights into your testing experience.
• Complete all testing assignments within set timelines.

Requirements

To be eligible, you must:

• Be at least 21 years old.
• Reside in one of the following states: Michigan, New Jersey, Pennsylvania, or West Virginia.
• Own a laptop or desktop computer.
• Be able to complete a short, paid online training and onboarding process.

No previous testing or gambling experience is needed. You will not be gambling with your own money, and there are no fees or out-of-pocket costs. All the interactions/game-play would be for testing purposes.

Compensation and Benefits

• Guaranteed earnings of at least $1,000 for approximately 20 hours of testing.
• Minimum of $25/hour, with higher pay for faster testers.
• $100 bonus upon completing the onboarding program.
• Flexible schedule – choose when you want to work.
• Work from home – test websites from the comfort of your own space.
• Fast payments – get paid after each of the 4 testing stages.
• Excellent support – coordinators available daily from 6 AM to 11 PM ET.

What Our Testers Say

"Great side gig for some extra cash. The team is very communicative and will answer any questions/concerns!" – Maria, Trustpilot (2021)

"Tasks are clearly explained with step-by-step instructions. You can work when it's convenient. Support is very helpful and responsive." – Anonymous, Glassdoor (2025)

Read more reviews on Glassdoor, Trustpilot, and Google.

Equal Opportunity Statement

Little Wheel LLC is proud to be an Equal Opportunity Employer. We are committed to creating an inclusive environment for all applicants and employees, regardless of race, religion, color, national origin, gender identity, sexual orientation, age, disability, or veteran status. We celebrate diversity and strive to create a workplace where everyone feels valued.

Company Info

Website: Address: Little Wheel LLC, 250 Pehle Ave, Suite 200, Saddle Brook, NJ 07663 Phone: (833) 313-7490

IDR is seeking a Project Manager to join one of our top clients for a fully remote opportunity. This role involves managing projects within the Talent Technology portfolio, supporting initiatives that often involve AI, RPA, and automation. The company operates within the technology and HR solutions industry, focusing on enhancing talent management processes.

Position Overview:

Working within the Talent team, the Project Manager is responsible for planning, coordination and execution of delivery aspects of assigned projects in support of initiatives within the Talent Technology portfolio. The PM is responsible for coordinating assignment of individual Talent Technology responsibilities, developing the project plan, tasks and deliverables to ensure timely tech team delivery.

• 8+ years of project management experience with the ability to effectively manage multiple projects with moderate to high risk for a large enterprise
• 4+ years of experience leading projects supporting AI, RPA, and automation intiatives across Talent and HR ecosystem
  • Projects around Co-Pilot Agents and Co-Pilot Studio (preferred)
• Experience in navigating in a matrix reporting environment solving/resolving complex issues

• PMP Certification

What's in it for you?

• Competitive compensation package
• Full Benefits; Medical, Vision, Dental, and more!
• Opportunity to get in with an industry leading organization.

Why IDR?

• 25+ Years of Proven Industry Experience in 4 major markets
• Employee Stock Ownership Program
• Dedicated Engagement Manager who is committed to you and your success.
• Medical, Dental, Vision, and Life Insurance
• ClearlyRated's Best of Staffing Client and Talent Award winner 12 years in a row.

Essential Functions:

• Knows, understands, incorporates and demonstrates the Trinity Mission, Vision and Values in behaviors, practices, standards policies procedures and decisions.
• Demonstrates understanding of appropriate clinical documentation to ensure the severity of illness, risk of mortality, quality indicators and level of services provided are accurately reflected in the health record.
• Communicates with and educates physicians and all other member of the healthcare team in clinical documentation and monitors provider engagement.
• Conducts concurrent reviews of selected patient health records to address legibility, clarity, completeness, consistency and precision of clinical documentation.
• Formulates compliant clarifications/queries following Trinity Health's documentation integrity procedures.

Minimum Qualifications:

• Must possess an Associate/Diploma Degree in Health Information Technology (HIT) or Advanced degree in nursing (NP, APN) or Physician Assistant. In absence of college degree, must have three (3) years' experience as an inpatient code or documentation specialist.
• Preferred Certifications: RN, RHIA, RHIT, CCS, CCDS or CDIP
• Experienced in critical care, medical or surgical inpatient care nursing as an RN, PA, NP, APN or inpatient coder preferred
• Excellent communication, interpersonal, collaboration and relationship building skills. Strong critical thinking skills, and ability integrate knowledge. Prioritization and organizations skills required.
• Demonstrated ability to use standardized desktop and Windows based computer system. Data entry and typing skills at minimum 30 wph.

Our Commitment

Rooted in our Mission and Core Values, we honor the dignity of every person and recognize the unique perspectives, experiences, and talents each colleague brings. By finding common ground and embracing our differences, we grow stronger together and deliver more compassionate, person-centered care. We are an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other status protected by federal, state, or local law.